B(C6F5)3‑Catalyzed Multicomponent Reactions of 2,3-Diketoesters, Amines, Allenes, and Nucleophiles: Synthesis of 2α-Functionalized Pyrroles

An efficient B­(C6F5)3-catalyzed multicomponent reaction of 2,3-diketoesters, amines, allenes, and nucleophiles was reported, which afforded 2α-functionalized pyrroles in moderate to good yields. The reaction features low catalyst loading, usage of a small amount of solvent, high atom economy, tunab...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 89; no. 17; pp. 12286 - 12297
Main Authors Zhang, Wei-Wei, Sha, Qiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.09.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DESIGN
VICINAL TRICARBONYL COMPOUNDS
CHEMISTRY
REVERSIBLE CROSS-LINKING
INHIBITORS
EFFICIENT
DERIVATIVES
NINHYDRIN
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Summary:An efficient B­(C6F5)3-catalyzed multicomponent reaction of 2,3-diketoesters, amines, allenes, and nucleophiles was reported, which afforded 2α-functionalized pyrroles in moderate to good yields. The reaction features low catalyst loading, usage of a small amount of solvent, high atom economy, tunable installation of diverse functional groups at 2α-position, and water being formed as the byproduct. This is the first multicomponent reaction that combines vicinal tricarbonyl compounds with allenes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01221